2-Amino-5-hydroxypyridine → HCID 90411099, Verbindung

HRID 626587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626587
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.CC(C)([O-])C.[K+].Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH:25]2[CH2:27][CH2:26]2)=[O:23])[CH:17]=1>CC(N(C)C)=O.CCOC(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([O:8][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH:25]3[CH2:26][CH2:27]3)=[O:23])[CH:17]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 42319722-Amino-5-hydroxypyridineHCID 23665647Potassium tert-butoxideHCID 256064754-Chloro-N-cyclopropylpyridine-2-carboxamide

Produkt 1

HCID 90411099HCID 90411099, VerbindungAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

A solution of 2-amino-5-hydroxypyridine (0.578 g, 5.25 mmol) in DMA (8.75 mL) was treated with potassium tert-butoxide (0.663 g, 5.90 mmol), stirred at RT for 1 h, treated with a solution of 4-chloro-N-cyclopropylpicolinamide (0.86 g, 4.37 mmol) in DMA (8.75 mL) and stirred at RT for 20 h. The mixture was diluted with EtOAc, washed with 1N NaOH, then brine and the organic layer was dried over Na2SO4, concentrated to dryness and purified by silica gel chromatography (MeOH/EtOAc) to afford 4-((6-aminopyridin-3-yl)oxy)-N-cyclopropylpicolinamide (0.674 g, 57%). 1H NMR (400 MHz, DMSO-d6): δ 8.72 (d, J=5.0 Hz, 1H), 8.44 (d, J=5.6 Hz, 1H), 7.82 (d, J=2.9 Hz, 1H), 7.31-7.30 (m, 2H), 7.11 (dd, J=5.6, 2.6 Hz, 1H), 6.53 (d, J=8.9 Hz, 1H), 6.08 (s, 2H), 2.85-2.84 (m, 1H), 0.65-0.62 (m, 4H); MS (ESI) m/z: 271.1 (M+H+).

Aufarbeitung

  1. stirringstirred at RT for 20 h
  2. washwashed with 1N NaOH
  3. dry with materialbrine and the organic layer was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. custompurified by silica gel chromatography (MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-2ab53b27fbfe49faab008a51ec2bec12
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309224B2

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